The present invention relates to C.sub.1 -C.sub.6 alkyl-2-methyl-3,4-pentadienoates, more particularly isobutyl-2-methyl-3,4-pentadienoate and n-hexyl-2-methyl-3,4-pentadienoate to alter the flavor and/or aroma of consumable materials, e.g., tobacco, foodstuffs, perfume compositions and perfumed articles.
There has been considerable work performed related to substances which can be used to impart (or enhance) flavors to (or in) various consumable materials. These substances are used to diminish the use of natural materials, some of which may be in short supply and to provide more uniform properties in the finished product. Sweet, fruity, winey, pear, strawberry, tagette oil-like and apple aromas as well as sweet, fruity, winey, strawberry, creamy, tagette oil-like, apple and pear tastes are particularly desirable for many uses in foodstuff flavors. Chamomile, fruity, wormwood and strawberry notes are desirable in perfume compositions. Fruity, sweet and woody notes are desirable in tobacco flavoring compositions.
U.S. Pat. No. 3,499,769 issued on Mar. 10, 1970 discloses processes for imparting a fresh fruity flavor (particularly strawberry flavor) to foods by adding a small amount of 2-methyl-2-pentenoic acid to the foodstuff. In U.S. Pat. No. 3,499,769 it is emphasized that the basic nuance imparted by 2-methyl-2-pentenoic acid is a "berry" flavor. Quite unexpectedly, the novel compositions of matter of the instant invention have properties different in kind from the 2-methyl-2-pentenoic acid of U.S. Pat. No. 3,499,769.
Methyl-2-methyl-3,4-pentadienoate and ethyl-2-methyl-3,4-pentadienoate are known compounds, but uses of these compounds taking advantage of their organoleptic properties, in foodstuffs, perfume compositions, perfumed articles and/or tobacco are not disclosed in the prior art.
Synthesis of ethyl-2-methyl-3,4-pentadienoate by means of reaction of propargyl alcohol with triethyl orthopropionate is disclosed by Crandall and Tindell, J.Chem.Soc. D 1970 (21), 1411-12.
Synthesis of methyl-2-methyl-3,4-pentadienotate by means of reaction of 3,4-pentadienoic acid with CH.sub.2 N.sub.2 (C.sub.2 H.sub.5).sub.2 O is disclosed by Ullman and Fanshawe, J.Am.Chem.Soc. 83, 2379-83 (1961).
Japanese Patent J75000022 (Tanabe Seiyaku Co. Ltd.) discloses aryl-alkyl 1,3-pentadiene-1-carboxylates useful as deodorants and antibacterial agents of the formula: EQU CH.sub.3 --CH.dbd.CH--CH.dbd.CH--C(O)--O(CH.sub.2).sub.n R
(where R is phenyl, alkylphenyl, alkoxyphenyl, dialkylamino phenyl or methylenedioxyphenyl, n is 1-3), as being prepared by condensing the corresponding acid with an aryl alkanol of the formula: EQU R(CH.sub.2).sub.n OH
in addition, British Pat. No. 1,379,038 published on Jan. 2, 1975 includes a broad disclosure of .gamma.,.delta. -unsaturated carbonyl compounds, useful as flavoring and odoriferous agents of the formula: ##STR1## (where m is 0 or 1; n=0 and the dotted line is a bond or n=1 and the dotted line is no bond; R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are each H, or linear or branched (a)cyclic, (un) saturated univalent hydrocarbon or oxygen-substituted hydrocarbon; or R.sup.7 with R.sup.3 or R.sup.4 or R.sup.5 may form a cycloaliphatic group, provided that R.sup.3 and R.sup.5 may not contain a multiple bond which is conjugated with the alpha, beta-bond) as being prepared by reacting an alpha-beta-unsaturated carbonyl compound (R.sup.5) (R.sup.3).sub.n C.dbd.C(C)--(O).sub.m --R.sup.7 or halogenated carbonyl compound X(R.sup.5) (R.sup.3).sub.n --CH(R.sup.4).sub.n --C(O)--R.sup.7 with an organometallic compound comprising a transition metal (preferred:Cu), an univalent cation (preferred-Li.sup.+) or [Mg-Halogen].sup.+ and an alkenyl radical R.sup.6 --C(R.sup.1).dbd.C(R.sup.2)--, preferred in the presence of a complexing agent e.g. diethyl ether, tetrahydrofuran, dimethoxyethane, N-tributylphosphine or trimethylphosphite.